Dimethylcarbamoyl Chloride → HCID 23349897, compound

HRID 614312Notes

Reaction equation

HRID 614312 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([N:12]([CH3:14])[CH3:13])[N:7]=1.[H-].[Na+].[CH3:18][N:19]([CH3:23])[C:20]([Cl:22])=[O:21].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:36].Cl>C1(C)C=CC=CC=1.C(O)C>[ClH:22].[ClH:36].[CH3:18][N:19]([CH3:23])[C:20]([N:5]([CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])[C:6]1[CH:11]=[N:10][CH:9]=[C:8]([N:12]([CH3:14])[CH3:13])[N:7]=1)=[O:21]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 23349871HCID 23349871, compound

Product 1

HCID 23349897HCID 23349897, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

2-(2-Dimethylaminoethylamino)-6-dimethylaminopyrazine (16.5 g., (0.079 mole) is dissolved in 150 ml dry toluene under nitrogen and sodium hydride (50% in mineral oil) (4.17 g., 0.087 mole) is added. The mixture is heated with stirring at 90°-98° C. for 1/2 hour and then refluxed for 1/2 hour. After cooling to 35° C. dimethylcarbamoylchloride (9.35 g., 0.087 mole) is added and the mixture is refluxed for 3 hours and cooled. Ethanol, 5 ml is added and the solvents are removed under reduced pressure. The residue is dissolved in dilute hydrochloric acid and extracted with ether. The aqueous layer is made alkaline with aqueous sodium hydroxide with a cooling bath to maintain the temperature below 35° C. The alkaline solution is extracted with methylene chloride. The organic extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under vacuum. The residual oil is dissolved in isopropanol, 50 ml and diethyl ether, 300 ml and then gaseous hydrogen chloride is passed into the solution. The product dihydrochloride crystallizes, is filtered, and washed with 100 ml of 1:1 acetone: isopropanol. Recrystallization from 150 ml isopropanol and 75 ml of diethyl ether yields 8 g. (0.029 mole) of the dihydrochloride salt, melting point 189° C. (dec).

Workup

  1. temperatureThe mixture is heated
  2. temperaturerefluxed for 1/2 hour
  3. additionis added
  4. temperaturethe mixture is refluxed for 3 hours
  5. temperaturecooled
  6. customthe solvents are removed under reduced pressure
  7. dissolutionThe residue is dissolved in dilute hydrochloric acid
  8. extractionextracted with ether
  9. temperatureto maintain the temperature below 35° C
  10. extractionThe alkaline solution is extracted with methylene chloride
  11. washThe organic extracts are washed with saturated sodium chloride solution
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated under vacuum
  14. dissolutionThe residual oil is dissolved in isopropanol
  15. customThe product dihydrochloride crystallizes
  16. filtrationis filtered
  17. washwashed with 100 ml of 1:1 acetone
  18. customRecrystallization from 150 ml isopropanol and 75 ml of diethyl ether
  19. customyields 8 g

Sources & evidence

ORD record
ord-a7dd33f7faef4785bc5247f5d0443272
Source dataset
uspto-grants-1979_03
Patent number
US04144338

Reaction notes

Loading…